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Pineapple Upside Down Cupcakes

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When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. These pineapple upside down cupcakes are delish.

There’s nothing quite like a tasty treat that is portable to make it all the more fun and exciting. These pineapple upside down cake cupcakes are easy to make and even easier to eat!

Try out this fun recipe for the summer today!

When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. These pineapple upside down cupcakes are delish.

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Cupcakes are all the rage!  These baby cakes are being served everywhere. You can find them on the dessert table at family meals or even at weddings.

It doesn’t surprise me that people love cupcakes. When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. 

And these pineapple upside down cupcakes are delicious. Pineapple Upside Down Cupcakes have become my husband’s new favorite dessert.

I’m a chocolate loving kind of girl, but can definitely eat my way through a few Pineapple Upside Down Cupcakes when the opportunity presents itself.

You will need a few simple ingredients to get you started:

Yellow Cake Mix (eggs, oil, water) Whatever your particular mix calls for


Brown Sugar

Crushed Pineapple

Maraschino Cherries 

Something to grease your cupcake tins with. (I use Crisco, but a good non-stick spray should work, too)

You will also need to have some wax paper on hand so you can invert the cupcakes onto the wax paper when releasing them. 

Pineapple Upside Down Cupcakes

Here are a few tips to make this recipe work better:

When mixing these cupcakes if your cake mix calls for the water you will be replacing it with the pineapple juice you drained from the can. If you don’t have enough juice just add water until you get to the right measurements.

Be sure your cupcake tins are well greased. This will prevent sticking. 

When you add the butter, brown sugar pineapple and cherry push it down with the back of a spoon so it’s an even layer. 

Put these on the middle oven rack. 

If you are using a dark pan reduce your cooking temperature by 25 degrees. 

Let the cupcakes cool for 5 mins before inverting them. 

Following those few tips will ensure that these cupcakes will be a new family favorite if you can keep them around long enough for everyone to try! 

Curious minds want to know, Do you eat the cherry on top of your pineapple upside down cake?

I do not! If it was a chocolate covered cherry I’d probably eat it. But it’s a big no on maraschino cherries for me!

Printable Pineapple Upside Down Cake Cupcakes Recipe:

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

Yield: 24
Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes

These easy pineapple upside down cake cupcakes are sure to be a hit. They're delcious, adorable, and portable!


  • 1/2 cup butter, melted
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 20 ounce can crushed pineapple drained
  • 1 box of your favorite yellow cake mix
  • 3 eggs
  • 1/3 cup oil
  • 1 1/3 cup pineapple juice


  1. Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F.
  2. Grease 24 muffin cups. (Try using shortening or a good non-stick spray)
  3. Line a work surface with waxed paper
  4. Spoon 1 teaspoon melted butter into the bottom of each muffin cup.
  5. Spoon 1 tablespoon brown sugar in each muffin cup.
  6. Press a maraschino cherry into the center of the brown sugar in each muffin cup.
  7. Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.
  8. Mix yellow cake mix as directed adding in your oil, eggs, etc.. replacing the water with pineapple juice until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
  9. Pour cake batter into the muffin cup, filling them almost to the top; do not overfill.
  10. Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
  11. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the wax paper to release. Serve with pineapple and cherry sides up.


The oil and eggs are listed in the ingredients because every yellow cake mix I have ever used calls for those ingredients in those measurements. You may have to adjsut the ingredients accordingly depending on the cake mix you use.

Crushed pineapple works best.

Nutrition Information
Yield 24 Serving Size 1
Amount Per Serving Calories 225Total Fat 8gSaturated Fat 3gTrans Fat 0gUnsaturated Fat 4gCholesterol 33mgSodium 202mgCarbohydrates 37gFiber 1gSugar 27gProtein 2g

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Ursa ~

Sunday 15th of September 2019

I've been making them for years ~ My fiancé' calls them PUDcakes. I usually dice up the cherries so that you get a small bit of it in each bite.

Cathy G

Tuesday 7th of May 2019

Mine stuck also. Used non stick pan and spray but they stuck pretty bad. They are not pretty like yours but taste great! I will lower my oven temp next time to see if that helps.


Wednesday 1st of May 2019

Just made them, have a problem with them sticking to the wax paper (I used parchment paper thinking it won't stick) but it did stick. Did I take them out of the muffin tin too soon. They look delicious and hubby said they taste delicious. So that's good. Left them in muffin tin little over 5 min about 6 or so. Lots of the brown sugar & pineapple stuck in tin also, used butter knife to spread on cupcakes. I did get 24 cupcakes so that's really good. Just want to know about the sticking to the paper issues. Thanks

Michele Brosius

Sunday 5th of May 2019

I normally use the non-stick or silicone muffin pans and grease them with non-stick spray so I don't see much sticking in the pan. (Maybe lower your oven temp 25 degrees) I've also never had them stick to the wax paper. Maybe non-stick spray on your parchment may help. Thanks


Saturday 13th of April 2019

I have been making Pineapple UpSide Down Cupcakes for several years. I always use a Pineapple Supreme Cake Mix I drain my can of pineapple and use that juice for the liquid requested to make the cake mix. Most always have enough juice but if not I just add water to the juice. Big hit when I take them to a function.


Monday 8th of April 2019

Can they be made ahead of time and eaten the next day or should they be eaten fresh out of the oven and warm?

Michele Brosius

Monday 8th of April 2019

We always make them ahead of time. I've never tried them warm, but we just may have too. Thanks!

This recipe or post is in no way authorized or associated with the Weight Watchers or myWW Program.

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